Photorearrangement of  o ‐Methoxystilbenoids in Acid Media | Zendy

Ho JinnHsuan | Zendy; Lin JuiHsien | Zendy; Ho TongIng | Zendy

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Photorearrangement of o ‐Methoxystilbenoids in Acid Media

Author(s) -

Ho JinnHsuan,

Lin JuiHsien,

Ho TongIng

Publication year - 2005

Publication title -

journal of the chinese chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.329

H-Index - 45

eISSN - 2192-6549

pISSN - 0009-4536

DOI - 10.1002/jccs.200500113

Subject(s) - chemistry , irradiation , catalysis , oxidative phosphorylation , oxidative damage , photochemistry , medicinal chemistry , organic chemistry , biochemistry , antioxidant , physics , nuclear physics

Photorearrangements of o ‐methoxystilbenoils ( 1a‐1c ) in acid media have been investigated. Irradiation of o ‐methoxystilbene ( 1c ), for example, could lead to three major rearrangement products: 2,3,4‐trihydrophenanthren‐1‐ones ( 2c ), trans ‐1‐arylbut‐2‐en‐1‐ones ( 3c ), and 1‐hydroxy‐9,10‐dihydrophenanthrenes ( 7 ). Further irradiation of trans ‐1‐arylbut‐2‐en‐1‐ones ( 3 ) could afford three more products ( 4 , 5 and 6 ). The key step for this photorearrangement is acid‐catalyzed formal [1,9] hydrogen shift. The products of the eliminative and oxidative photoreaction were also obtained; the formation of the oxidative product is due to the fact that the unfavorable methoxy group in the intermediate DHP‐3 retards the rate of acid‐catalyzed formal [1,9] hydrogen shift.

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